NPASS Compound

Structure

NPC123544 OpenBabel07101718242D 37 41 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 17 2 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 29 2 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 26 35 2 0 0 0 0 27 28 1 0 0 0 0 27 36 1 1 0 0 0 28 17 1 6 0 0 0 28 37 1 0 0 0 0 29 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.15
Volume:	503.406
LogP:	3.649
LogD:	0.992
LogS:	-2.705
# Rotatable Bonds:	5
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	3.715
Fsp3:	0.138
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.142
MDCK Permeability:	5.2659943321486935e-06
Pgp-inhibitor:	0.283
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.747
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	98.68225860595703%
Volume Distribution (VD):	0.35
Pgp-substrate:	2.2846126556396484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.547
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.989
CYP2D6-inhibitor:	0.707
CYP2D6-substrate:	0.598
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.827

ADMET: Excretion

Clearance (CL):	8.238
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.953
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.889
Respiratory Toxicity:	0.029

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC123544

Natural Product ID:	NPC123544
*Common Name:**	Gericudranin D
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(4-hydroxyphenyl)methyl]-2,3-dihydrochromen-4-one
Synonyms:	Gericudranin D
Standard InCHIKey:	LHFMOLHENFWCMZ-WUFINQPMSA-N
Standard InCHI:	InChI=1S/C29H24O8/c30-18-7-1-15(2-8-18)13-21-24(33)22(14-16-3-9-19(31)10-4-16)29-23(25(21)34)26(35)27(36)28(37-29)17-5-11-20(32)12-6-17/h1-12,27-28,30-34,36H,13-14H2/t27-,28+/m0/s1
SMILES:	Oc1ccc(cc1)Cc1c(O)c(Cc2ccc(cc2)O)c(c2c1O[C@H](c1ccc(cc1)O)[C@H](C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510170
PubChem CID:	44559901
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	5
IC50	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT390	Cell Line	LOX IMVI	Homo sapiens	ED50	=	16.6	ug ml-1	PMID[532262]
NPT5528	Cell Line	MOLT-4F	Homo sapiens	ED50	=	8.9	ug ml-1	PMID[532262]
NPT386	Cell Line	KM12	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[532262]
NPT371	Cell Line	UO-31	Homo sapiens	ED50	=	5.2	ug ml-1	PMID[532262]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[532263]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	9.5	ug ml-1	PMID[532262]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC123544 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1695
0.2-0.3	4120
0.3-0.4	9976
0.4-0.5	8323
0.5-0.6	3835
0.6-0.7	5646
0.7-0.8	4825
0.8-0.85	2677
0.85-0.9	967
0.9-0.95	202
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC63438
0.9733	High Similarity	NPC20907
0.9733	High Similarity	NPC244250
0.9603	High Similarity	NPC268193
0.9539	High Similarity	NPC304745
0.9539	High Similarity	NPC111341
0.9481	High Similarity	NPC295090
0.9474	High Similarity	NPC109594
0.9474	High Similarity	NPC112701
0.9474	High Similarity	NPC326592
0.947	High Similarity	NPC262038
0.947	High Similarity	NPC319910
0.947	High Similarity	NPC328740
0.947	High Similarity	NPC477897
0.947	High Similarity	NPC209846
0.947	High Similarity	NPC262039
0.947	High Similarity	NPC278476
0.947	High Similarity	NPC254412
0.947	High Similarity	NPC289774
0.9416	High Similarity	NPC475184
0.9412	High Similarity	NPC259710
0.9412	High Similarity	NPC48579
0.9412	High Similarity	NPC304207
0.9412	High Similarity	NPC217706
0.9412	High Similarity	NPC134171
0.9412	High Similarity	NPC300668
0.9412	High Similarity	NPC182555
0.9412	High Similarity	NPC66441
0.9412	High Similarity	NPC207809
0.9408	High Similarity	NPC150123
0.9408	High Similarity	NPC171651
0.9408	High Similarity	NPC161881
0.9408	High Similarity	NPC35567
0.9408	High Similarity	NPC138288
0.9408	High Similarity	NPC244583
0.9408	High Similarity	NPC56232
0.9408	High Similarity	NPC217149
0.9408	High Similarity	NPC216035
0.9408	High Similarity	NPC10807
0.9408	High Similarity	NPC174086
0.9408	High Similarity	NPC243171
0.9404	High Similarity	NPC105136
0.94	High Similarity	NPC122894
0.9375	High Similarity	NPC257667
0.9375	High Similarity	NPC472454
0.9375	High Similarity	NPC186847
0.9367	High Similarity	NPC82330
0.9351	High Similarity	NPC10754
0.9351	High Similarity	NPC32867
0.9351	High Similarity	NPC208152
0.9351	High Similarity	NPC20530
0.9351	High Similarity	NPC78492
0.9351	High Similarity	NPC69531
0.9351	High Similarity	NPC215917
0.9346	High Similarity	NPC248793
0.9346	High Similarity	NPC293286
0.9346	High Similarity	NPC180301
0.9338	High Similarity	NPC3642
0.9313	High Similarity	NPC287884
0.9313	High Similarity	NPC8704
0.9308	High Similarity	NPC260266
0.929	High Similarity	NPC257166
0.9281	High Similarity	NPC115601
0.9281	High Similarity	NPC78324
0.9281	High Similarity	NPC39154
0.9281	High Similarity	NPC475790
0.9281	High Similarity	NPC208011
0.9276	High Similarity	NPC124478
0.9276	High Similarity	NPC177308
0.925	High Similarity	NPC475212
0.925	High Similarity	NPC53252
0.925	High Similarity	NPC107627
0.9236	High Similarity	NPC142252
0.9236	High Similarity	NPC97812
0.9236	High Similarity	NPC289771
0.9231	High Similarity	NPC51760
0.9231	High Similarity	NPC15815
0.9231	High Similarity	NPC51247
0.9226	High Similarity	NPC471787
0.9221	High Similarity	NPC223701
0.9221	High Similarity	NPC88983
0.9221	High Similarity	NPC236756
0.9221	High Similarity	NPC7989
0.9221	High Similarity	NPC472583
0.9221	High Similarity	NPC311579
0.9221	High Similarity	NPC121568
0.9216	High Similarity	NPC471677
0.9216	High Similarity	NPC263384
0.9216	High Similarity	NPC244577
0.9216	High Similarity	NPC474023
0.9216	High Similarity	NPC472420
0.9216	High Similarity	NPC472422
0.9216	High Similarity	NPC471676
0.9216	High Similarity	NPC474021
0.9211	High Similarity	NPC89442
0.9205	High Similarity	NPC40086
0.9205	High Similarity	NPC176869
0.9205	High Similarity	NPC3779
0.9205	High Similarity	NPC476182
0.9205	High Similarity	NPC122828
0.9205	High Similarity	NPC211466
0.9205	High Similarity	NPC44721
0.92	High Similarity	NPC470135
0.92	High Similarity	NPC142731
0.92	High Similarity	NPC279417
0.92	High Similarity	NPC62290
0.92	High Similarity	NPC208176
0.92	High Similarity	NPC326506
0.92	High Similarity	NPC49130
0.92	High Similarity	NPC306607
0.92	High Similarity	NPC39045
0.92	High Similarity	NPC470136
0.92	High Similarity	NPC4152
0.9182	High Similarity	NPC7154
0.9182	High Similarity	NPC125039
0.9182	High Similarity	NPC72787
0.9182	High Similarity	NPC36
0.9182	High Similarity	NPC7688
0.9182	High Similarity	NPC58223
0.9182	High Similarity	NPC36916
0.9177	High Similarity	NPC259834
0.9177	High Similarity	NPC131745
0.9177	High Similarity	NPC219927
0.9177	High Similarity	NPC477841
0.9172	High Similarity	NPC306978
0.9167	High Similarity	NPC1796
0.9161	High Similarity	NPC476169
0.9161	High Similarity	NPC258474
0.9161	High Similarity	NPC201227
0.9161	High Similarity	NPC477958
0.9161	High Similarity	NPC470681
0.9156	High Similarity	NPC210597
0.9145	High Similarity	NPC218569
0.9145	High Similarity	NPC10097
0.9139	High Similarity	NPC470132
0.9139	High Similarity	NPC472629
0.9139	High Similarity	NPC228779
0.9139	High Similarity	NPC148011
0.9139	High Similarity	NPC470133
0.9139	High Similarity	NPC470131
0.9139	High Similarity	NPC1940
0.9139	High Similarity	NPC473078
0.9139	High Similarity	NPC109183
0.9139	High Similarity	NPC470134
0.9136	High Similarity	NPC477529
0.9125	High Similarity	NPC320741
0.9125	High Similarity	NPC224851
0.9125	High Similarity	NPC171985
0.9119	High Similarity	NPC179198
0.9119	High Similarity	NPC183672
0.9119	High Similarity	NPC290160
0.9119	High Similarity	NPC66087
0.9119	High Similarity	NPC278419
0.9114	High Similarity	NPC312273
0.9114	High Similarity	NPC47923
0.9114	High Similarity	NPC471499
0.9114	High Similarity	NPC470125
0.9114	High Similarity	NPC301256
0.9108	High Similarity	NPC117418
0.9108	High Similarity	NPC105584
0.9108	High Similarity	NPC22192
0.9108	High Similarity	NPC53545
0.9103	High Similarity	NPC198489
0.9103	High Similarity	NPC61112
0.9103	High Similarity	NPC146636
0.9103	High Similarity	NPC309648
0.9097	High Similarity	NPC469405
0.9097	High Similarity	NPC71061
0.9097	High Similarity	NPC209760
0.9097	High Similarity	NPC290830
0.9097	High Similarity	NPC72425
0.9097	High Similarity	NPC194593
0.9097	High Similarity	NPC303485
0.9097	High Similarity	NPC100134
0.9091	High Similarity	NPC138299
0.9091	High Similarity	NPC67322
0.9091	High Similarity	NPC222713
0.9091	High Similarity	NPC111112
0.9091	High Similarity	NPC472636
0.9085	High Similarity	NPC307052
0.9085	High Similarity	NPC132345
0.9085	High Similarity	NPC472628
0.9085	High Similarity	NPC291746
0.9085	High Similarity	NPC288840
0.9085	High Similarity	NPC139966
0.908	High Similarity	NPC168789
0.9079	High Similarity	NPC472918
0.9079	High Similarity	NPC472627
0.9079	High Similarity	NPC21835
0.9074	High Similarity	NPC102277
0.9074	High Similarity	NPC279209
0.9073	High Similarity	NPC470890
0.9073	High Similarity	NPC87486
0.9073	High Similarity	NPC124780
0.9062	High Similarity	NPC477840
0.9057	High Similarity	NPC476247
0.9057	High Similarity	NPC473012
0.9057	High Similarity	NPC44947
0.9057	High Similarity	NPC473011
0.9051	High Similarity	NPC470326

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC123544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	919
0.2-0.3	1753
0.3-0.4	2644
0.4-0.5	1856
0.5-0.6	1014
0.6-0.7	380
0.7-0.8	132
0.8-0.85	31
0.85-0.9	18
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9276	High Similarity	NPD4380	Phase 2
0.9182	High Similarity	NPD6168	Clinical (unspecified phase)
0.9182	High Similarity	NPD6166	Phase 2
0.9182	High Similarity	NPD6167	Clinical (unspecified phase)
0.9045	High Similarity	NPD7075	Discontinued
0.9012	High Similarity	NPD7804	Clinical (unspecified phase)
0.8947	High Similarity	NPD4378	Clinical (unspecified phase)
0.8924	High Similarity	NPD4381	Clinical (unspecified phase)
0.8917	High Similarity	NPD8443	Clinical (unspecified phase)
0.8875	High Similarity	NPD6959	Discontinued
0.8854	High Similarity	NPD2393	Clinical (unspecified phase)
0.8854	High Similarity	NPD7096	Clinical (unspecified phase)
0.879	High Similarity	NPD6801	Discontinued
0.8733	High Similarity	NPD1550	Clinical (unspecified phase)
0.8733	High Similarity	NPD1552	Clinical (unspecified phase)
0.8726	High Similarity	NPD7411	Suspended
0.8712	High Similarity	NPD7852	Clinical (unspecified phase)
0.8701	High Similarity	NPD7410	Clinical (unspecified phase)
0.8675	High Similarity	NPD1549	Phase 2
0.8675	High Similarity	NPD7993	Clinical (unspecified phase)
0.8671	High Similarity	NPD1934	Approved
0.8563	High Similarity	NPD6797	Phase 2
0.8512	High Similarity	NPD7251	Discontinued
0.8509	High Similarity	NPD4868	Clinical (unspecified phase)
0.8503	High Similarity	NPD7074	Phase 3
0.8471	Intermediate Similarity	NPD5403	Approved
0.8462	Intermediate Similarity	NPD7808	Phase 3
0.8443	Intermediate Similarity	NPD7054	Approved
0.8408	Intermediate Similarity	NPD1512	Approved
0.8397	Intermediate Similarity	NPD6799	Approved
0.8395	Intermediate Similarity	NPD7768	Phase 2
0.8393	Intermediate Similarity	NPD7472	Approved
0.8355	Intermediate Similarity	NPD1510	Phase 2
0.8353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD5401	Approved
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD5402	Approved
0.8301	Intermediate Similarity	NPD2796	Approved
0.8294	Intermediate Similarity	NPD6559	Discontinued
0.8282	Intermediate Similarity	NPD3882	Suspended
0.828	Intermediate Similarity	NPD1511	Approved
0.8274	Intermediate Similarity	NPD3818	Discontinued
0.8272	Intermediate Similarity	NPD7819	Suspended
0.8272	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD5494	Approved
0.8121	Intermediate Similarity	NPD3749	Approved
0.8118	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD8312	Approved
0.8092	Intermediate Similarity	NPD8313	Approved
0.8079	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD8455	Phase 2
0.8036	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1607	Approved
0.7937	Intermediate Similarity	NPD7390	Discontinued
0.7929	Intermediate Similarity	NPD3787	Discontinued
0.7862	Intermediate Similarity	NPD3750	Approved
0.7849	Intermediate Similarity	NPD3751	Discontinued
0.7843	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2800	Approved
0.7772	Intermediate Similarity	NPD6776	Approved
0.7772	Intermediate Similarity	NPD6779	Approved
0.7772	Intermediate Similarity	NPD6778	Approved
0.7772	Intermediate Similarity	NPD6777	Approved
0.7772	Intermediate Similarity	NPD6781	Approved
0.7772	Intermediate Similarity	NPD6782	Approved
0.7772	Intermediate Similarity	NPD6780	Approved
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7712	Intermediate Similarity	NPD4908	Phase 1
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7435	Discontinued
0.7643	Intermediate Similarity	NPD6651	Approved
0.7628	Intermediate Similarity	NPD1613	Approved
0.7628	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1465	Phase 2
0.7614	Intermediate Similarity	NPD5953	Discontinued
0.7613	Intermediate Similarity	NPD6798	Discontinued
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2935	Discontinued
0.7606	Intermediate Similarity	NPD7871	Phase 2
0.7606	Intermediate Similarity	NPD7870	Phase 2
0.7596	Intermediate Similarity	NPD4360	Phase 2
0.7596	Intermediate Similarity	NPD4363	Phase 3
0.7576	Intermediate Similarity	NPD920	Approved
0.7572	Intermediate Similarity	NPD3926	Phase 2
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2533	Approved
0.7561	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2534	Approved
0.7561	Intermediate Similarity	NPD2532	Approved
0.7558	Intermediate Similarity	NPD1247	Approved
0.7556	Intermediate Similarity	NPD8150	Discontinued
0.7553	Intermediate Similarity	NPD7698	Approved
0.7553	Intermediate Similarity	NPD7696	Phase 3
0.7553	Intermediate Similarity	NPD7697	Approved
0.7547	Intermediate Similarity	NPD3748	Approved
0.7546	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD919	Approved
0.7539	Intermediate Similarity	NPD8151	Discontinued
0.7526	Intermediate Similarity	NPD7584	Approved
0.7516	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3226	Approved
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1243	Approved
0.7453	Intermediate Similarity	NPD2344	Approved
0.7452	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7874	Approved
0.7405	Intermediate Similarity	NPD943	Approved
0.738	Intermediate Similarity	NPD7699	Phase 2
0.738	Intermediate Similarity	NPD7700	Phase 2
0.7378	Intermediate Similarity	NPD6190	Approved
0.7372	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7801	Approved
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD1610	Phase 2
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7358	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5124	Phase 1
0.7356	Intermediate Similarity	NPD7199	Phase 2
0.7329	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.7308	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2424	Discontinued
0.7294	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1203	Approved
0.7284	Intermediate Similarity	NPD6099	Approved
0.7284	Intermediate Similarity	NPD6100	Approved
0.7284	Intermediate Similarity	NPD5408	Approved
0.7284	Intermediate Similarity	NPD5404	Approved
0.7284	Intermediate Similarity	NPD5405	Approved
0.7284	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD2309	Approved
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD6355	Discontinued
0.7247	Intermediate Similarity	NPD7228	Approved
0.7246	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8320	Phase 1
0.724	Intermediate Similarity	NPD8319	Approved
0.7239	Intermediate Similarity	NPD2346	Discontinued
0.7232	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7215	Intermediate Similarity	NPD3027	Phase 3
0.7212	Intermediate Similarity	NPD7003	Approved
0.7211	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4287	Approved
0.7181	Intermediate Similarity	NPD4361	Phase 2
0.7181	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7097	Phase 1
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7151	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7129	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7585	Approved
0.7127	Intermediate Similarity	NPD3823	Discontinued
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4966	Approved
0.7119	Intermediate Similarity	NPD5710	Approved
0.7119	Intermediate Similarity	NPD5711	Approved
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7118	Intermediate Similarity	NPD1653	Approved
0.7117	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7212	Phase 2
0.7083	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7213	Phase 3
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7077	Intermediate Similarity	NPD7583	Approved
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6212	Phase 3
0.7074	Intermediate Similarity	NPD6213	Phase 3
0.7063	Intermediate Similarity	NPD3268	Approved
0.7056	Intermediate Similarity	NPD7177	Discontinued
0.7052	Intermediate Similarity	NPD6844	Discontinued
0.7041	Intermediate Similarity	NPD4661	Approved
0.7041	Intermediate Similarity	NPD4662	Approved
0.7041	Intermediate Similarity	NPD7447	Phase 1
0.7039	Intermediate Similarity	NPD2403	Approved
0.7039	Intermediate Similarity	NPD4575	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data